Water-soluble polyhydroxyaminoether and process for preparing the same

Abstract

A water soluble polymer comprising a copolyhydroxyaminoether having side-chains of polyalkylene oxides, an aqueous solution of said polymer and process for preparing the copolyhydroxyaminoether.

1 . A water-soluble polymer comprising a copolyhydroxyaminoether having side-chains of polyalkylene oxides.  
     
     
         2 . The polymer of  claim 1  represented by the formula:  
       
         
           
           
               
               
           
         
       
       wherein R is hydrogen or C 1 -C 20  alkyl; R 1  is individually an aromatic or substituted aromatic moiety; Y is an organic moiety that does not contain an epoxy group and Z is an organic moiety, optionally containing an epoxy group; x is 0-0.99; and n is 5-400; each A is individually an amino group represented by one of the formulas:  
       
         
           
           
               
               
           
         
       
       wherein R 2  is hydrocarbyl or substituted hydrocarbyl; R 3  is C 2 -C 10  hydrocarbylene or substituted hydrocarbylene; R 4  is C 2 -C 20  hydrocarbylene or substituted hydrocarbylene, wherein the substituent(s) is hydroxyl, cyano, halo, arlyloxy, alkylamido, arylamido, alkylcarbonyl, or arylcarbonyl; and each B is represented by the formula:  
       
         
           
           
               
               
           
         
       
       wherein R 5  is hydrocarbyl; each R 6  is individually hydrogen, methyl, ethyl, hydrocarbyl or combinations (change made for consistency) thereof; and x is 0-0.99 when q is greater than 40 but less than 0.2 or greater than 0.8 when q is less than 40.  
     
     
         3 . The polymer of  claim 2  wherein R is hydrogen; each R 1  is individually isopropylidenediphenylene, 1,4-phenylene, 1,3-phenylene, methylenediphenylene, thidodiphenylene, carbonyldiphenylene, or combinations thereof; each R 2  is individually methyl, ethyl, phenyl, benzyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-(acetamido)ethyl, or combinations thereof; R 3  and R 4  are individually (change made for consistency) ethylene, 1,2-propylene, 1,2-butylene, or combinations thereof; and R 5  is C 1 -C 20  alkyl; R 6  is a mixture of hydrogen and methyl; each of Y and Z are individually bis(2-hydroxyethyl)amino or N-(2-hydroxyethyl)piperazinyl; q is 20-50, and n is 10-25.  
     
     
         4 . The polymer of  claim 3  wherein R 1  is isopropylidenediphenylene and R 2  is 2-hydroxyethyl.  
     
     
         5 . The polymer of  claim 3  wherein each R 5  is individually hydrogen, methyl, ethyl, propyl, butyl, benzyl or combinations thereof; Y and Z are bis(2-hydroxyethyl)amino.  
     
     
         6 . A process for preparing a water-soluble polymer which comprises (1) reacting an equivalent or excess of a difunctional amine or mixtures thereof with an excess or equivalent amount of a diglycidyl ether of a bisphenol or mixtures thereof, optionally in the presence of a monofunctional nucleophile and optionally in the presence of a catalyst and/or a solvent; or (2) reacting an equivalent or excess of a difunctional amine or mixtures thereof with an excess or equivalent amount of a diglycidyl ether of a bisphenol or mixtures thereof, optionally in the presence of a monofunctional nucleophile which functions as a terminating agent and, optionally, in the presence of a catalyst and/or a solvent; or (3) dissolving in an organic or non-organic solvent an amine selected from the group consisting of primary amine, a bis(secondary) diamine, or a mono-amine-functionalized poly(alkylene oxide) or mixtures thereof, adding to the amine solution a diglycidyl ether in an amine hydrogen equivalent to epoxide equivalent ratio of from 0.9:1 to 1.2:1 under conditions sufficient to cause the amine moieties to react with the epoxy moieties to form a polymer backbone having amine linkages, ether linkages and pendant hydroxyl moieties.  
     
     
         7 . The process of  claim 6  wherein the non-organic solvent is water and the monofunctional nucleophile is selected from the group consisting of a secondary amine, hydrogen sulfide, ammonia, ammonium hydroxide, a monofunctional phenol, an aryloxide salt, a carboxylic acid, a carboxylic acid salt, a mercaptan, and thiolate salt.  
     
     
         8 . The process of  claim 6  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
       
         
           
           
               
               
           
         
       
       wherein R 5 , R 6  and q are as defined above; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.  
     
     
         9 . The process of  claim 6  wherein the monofunctional nucleophile is selected from the group consisting of diethanolamine, N-(2-hydroxyethyl)piperazine, piperadine, diethylamine, dipropylamine, and dibenzylamine.  
     
     
         10 . The process-of  claim 6  wherein the monofunctional nucleophile is selected from the group consisting of phenol, acetic acid and propanoic acid and the catalyst is selected from the group consisting of a phosphonium or ammonium salt.  
     
     
         11 . The process of  claim 6  wherein the solvent is selected from the group consisting of 1-methyl-2-pyrrolidone, N,N-dimethylacetamide, water, diglyme, triglyme, diethylene glycol ethyl ether, diethylene glycol methyl ether, or propylene glycol methyl ether.  
     
     
         12 . A water-soluble polymer prepared by the process of  claim 6 .  
     
     
         13 . A composition comprising an aqueous fluid and the water-soluble polymer of  claim 1 .  
     
     
         14 . An aqueous solution comprising a polymer represented by the formula:  
       
         
           
           
               
               
           
         
       
       wherein each R is individually hydrogen or C 1 -C 20  alkyl; R 1  is an aromatic or substituted aromatic moiety; Y is an organic moiety that does not contain an epoxy group and Z is an organic moiety, optionally containing an epoxy group; x is 0-0.99; and n is 5-400; each A is individually an amino group represented by one of the formulas:  
       
         
           
           
               
               
           
         
       
       wherein R 2  is hydrocarbyl or substituted hydrocarbyl; R 3  is C 2 -C 10  hydrocarbylene or substituted hydrocarbylene; R 4  is C 2 -C 20  hydrocarbylene or substituted hydrocarbylene; and each B is represented by the formula:  
       
         
           
           
               
               
           
         
       
       wherein R 5  is hydrocarbyl; each R 6  is individually hydrogen, methyl, ethyl, hydrocarbyl or mixtures thereof; and x is 0-0.99 when q is greater than 40, but less than 0.2 or greater than 0.8 when q is less than 40.  
     
     
         15 . The aqueous solution of  claim 14  wherein in the formula representing the polymer, R is hydrogen; each R 1  is individually isopropylidenediphenylene, 1,4-phenylene, 1,3-phenylene, methylenediphenylene, thidodiphenylene, carbonyldiphenylene, or combinations thereof; each R 2  is individually methyl, ethyl, phenyl, benzyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-(acetamido)ethyl, or combinations thereof; R 3  and R 4  are individually ethylene, 1,2-propylene, 1,2-butylene, or combinations thereof; and R 5  is C 1 -C 20  alkyl.  
     
     
         16 . The aqueous solution of  claim 14  wherein viscosity increases as temperature is increased.  
     
     
         17 . A process which comprises dissolving the polymer of  claim 1  in water, the water optionally containing acids, bases, salts, solvents, or mixtures thereof.